The 20-Something Quarter Life Crisis, Getting Cast On Reality TV, And More With Big Brother Winner Dan Gheesling

Thought Catalog: You’ve got a lot going on in the social network world, how did you gain such a big following?

Dan Gheesling: You know, I’m fortunate to have been on a reality TV show that ran live. My wife (who worked in PR) and I talked about a business plan to execute while I was gone. To grow all of my social media, she took control of my Twitter, blog and Facebook, updating them with preset content. There were scheduled posts that I wrote, or videos I had filmed prior to heading on the show, so that when I got out I’d have to opportunity to create my own, new opportunities that aren’t solely tied to Big Brother.TC: Is there a reason for that?

DG: Let’s face it, I love the show but six months from now people aren’t still going to want to talk to me about Big Brother 14. The hard work that my wife Chelsea put in is allowing me to ride the wave of social media, and do things I’m passionate about – especially since I’m fortunate enough to have a very engaged audience.

TC: What have you been doing with that audience since the show?

DG: I’ve been coaching people one on one. People call it life coaching, but I hate that term. It’s just helping people one on one, tackling anything from a person running businesses, to a writer trying to finish a book. Also, I’m a big fan of videogames and there’s this thing called TwitchTV, which allows me to stream myself playing videogames. It’s just me having a lot of fun with my little community. Then the other thing I’m really focusing on is developing new content for my blog and to help people get cast on reality TV.

TC: Is there a golden rule or crucial tip we should know about how to get cast on reality TV?

DG: You’ve got to have a very compelling story. Most people who get on reality TV are outrageous – they’ve got wild hair, are physically built, or have something crazy about them. If you’re an average person, you’ve just got to have a dynamic story and pitch yourself as a character. Looking into a camera and telling the world how great you are is not natural for most people.

TC: So Dan, being that you’re in your twenties –

DG: (laughing) Barely! Thanks for reminding me.

TC: Did you ever have a twenty-something, quarter life crisis moment?

DG: I think I lived it on reality television! Not a crisis, but more so, I was 24 or 25, went on a show and won a half million dollars and earned a bit of pseudo fame. I use the term pseudo fame because it’s not real. You’re recognized here and there, but the bottom line is, it’s very fleeting. So if I had to choose something closest to a personal quarter life crisis, it’d be being thrust into a new environment, uncertain what was best to do. I think dealing with that at 25 was difficult. So that’s how I define it, without really defining it.

TC: Did you have any trouble finding your calling before reality TV altered plans?

DG: That’s something I struggled with. Everything is laid out in front of you: go to school, get a job, work at that job for 25 years or so. At some point along the way, that wasn’t enough for me.

TC: What changed that?

DG: There are two things that altered my life path if we take reality TV out of the equation. One was reading a book called Rich Dad, Poor Dad. It changes the way you think about your career and making money. It’s a simple concept but you’re never taught it. The other big thing was a blog called “Smart Passive Income.” It was created by a guy in his mid-20s who had just been laid off from his job. He decided to take a year trying to make money online, and he documented the experiment. This guy was very transparent, and he actually influenced and taught me how to write my first book. That blog and that book completely changed, and helped me define the career path I wanted to go on.

TC: Have you considered doing more writing online?

DG: For me I have the entrepreneur’s curse where there are so many different things I want to do. My blog is a work in progress, but there are things I’m really passionate about, and it’s a matter of making sense of those things in the blog.

TC: What are those passions?

DG: Coaching is one – I want to share those stories and do so in a way that people can apply it to their life. There’s a lot of regurgitated, self-health stuff out there, and I’d rather write about something I’ve actually done to help somebody.

TC: As far as writing and creating, how do you get comfortable sharing your work with the public?

DG: The more you put yourself out there, the more feedback you get, positive and negative. The first blog post I published I was freaking out – will people love it or hate it? But I started to learn that it doesn’t matter. The people who support you, that’s who you’ve got to focus on. There’ll always be the people who say, “That post was stupid, why’d you do this or that?” You can’t worry about them.

TC: So ideally what do you hope to accomplish?

DG: I know it sounds a little cheesy, but just to be able to do what I enjoy doing, while providing value to people and supporting my family. I’ve been fortunate to build an audience quickly from being on a show, and now I’m experimenting on how to provide value to them, and hearing what it is that they want.

TC: So far what are you most proud of?

DG: Business wise or life wise?

TC: Both.

DG: Well life wise without a doubt is finding, dating, courting and getting married to my wife Chelsea. Everyone I had met I couldn’t see myself spending my life with. It’s really difficult to find that person, and I just feel fortunate that I was able to find her… and not screw it up.

TC: And business wise?

DG: Businesswise I think coming to grips with, and being confident enough to not have a 9-5 job. For entrepreneurs when you first start, it’s very difficult – at least for me it was – to explain to people that you’re not working 9-5. They’re like, “Well what do you do?” And at some point, either a person gets it or they don’t – but whether or not they can grasp how you make a living, it shouldn’t effect what you enjoy doing. So I’d say building the confidence to look someone in the face and say “this is what I do” – and if they understand, cool, but if not, that doesn’t bother me either.

TC: What would the Dan Gheesling mission statement be?

DG: To provide as much value to the people who’ve shown interest and supported me over the years — in multiple ways! Whether through motivating, entertaining or having ‘em laugh at me, I just feel so fortunate. There are these people who make a choice to support me – if someone follows me on Twitter, I don’t take that lightly. I’m obsessed with trying to find ways to give back to them.

TC: If there were a piece of advice you could give to 20-somethings who are struggling to accomplish dreams, what would it be?

DG: The best advice I can offer is to reach out to someone they’d like to emulate. We’re often scared to ask for help. If there’s someone in a position you want to be in, you may have to reach out to them, and 10 similar people. Whenever I’ve asked for help from someone to guide me – you’d be surprised how willing people are.

TC: Time for a random question runoff, for the Big Brother fans and those who want to know you better. Sound good?

DG: Go for it!

TC:What kind of car do you drive?

DG: (laughing) I’m so glad you asked me this! A silver, 2005 – with spoiler – Ford Taurus, that now has 111,000 miles on it. It kind of defines me and it touches on what’s discussed in Rich Dad, Poor Dad. It’s the car I had before I won Big Brother, but it gets from point A to point B, and that’s what matters to me.

TC:What CD is currently in that car?

DG: Either a mix or Weezer’s Red album.

TC:What’s the last book you read?

DG: I’m currently reading Tribes: We Need You to Lead Us by Seth Godin.